Rick Astley’s 1987 hit song “Never Gonna Give You Up” became a viral Internet prank. Now he’s back, with his first U.S. release in twenty-three years.

Overlooked amid the Melania Trump plagiarism scandal at this summer’s Republican National Convention was an even stranger mystery. In the same speech in which she cribbed lines from Michelle Obama, Trump said of her husband, “He will never, ever give up. And, most importantly, he will never, ever let you down.” For a certain segment of the population, those words triggered a Pavlovian synth beat. Was it possible that Trump was sampling the 1987 Rick Astley song “Never Gonna Give You Up”?

“Maybe,” Astley said recently, in a booth in the balcony of the Box, on Chrystie Street. “I didn’t think so at first, because it wasn’t that blatant. If she’d said, ‘He’s never gonna run around and desert you,’ then I would have been in.” But the song has had a bizarre enough afterlife that anything seems plausible. In 2008, Astley, who lives outside London, was vacationing on the Amalfi Coast when a friend in Los Angeles sent him an e-mail with a link. When Astley clicked on it—surprise!—up came his own twenty-year-old music video for “Never Gonna Give You Up.” This was his first exposure to “rickrolling,” a viral Internet prank in which someone describes a link as one thing, when in fact it clicks through to the Astley video (which, consequently, now has more than two hundred and forty million views on YouTube).

Something about the song’s catchiness, its eighties-kitsch factor, and its utter randomness makes it ripe for Dadaist humor. There’s a video mashup of clips of President Obama in which he appears to be reciting the lyrics. In 2009, some M.I.T. students plastered the first seven notes of the chorus on the dome of the engineering library, thus rickrolling anyone in Cambridge who could read music.

“Listen, it’s a weird thing,” Astley said, using his go-to adjective for most things that have happened to him. At the Box, he wore a leather jacket and drank a cappuccino, as roadies sound-checked below. That night, he was performing his first concert in New York City since 1989. It was a preview of his Town Hall gig, on October 6th, in connection with his new album, “50,” his first release in the U.S. since he abruptly quit show business, twenty-three years ago. The Box concert, he explained, was “just to say, ‘Look, Rick’s still alive.’ ”

Astley was nineteen when he was discovered by the music producer Pete Waterman, who saw him singing with the band FBI. “Never Gonna Give You Up,” from his début album, became the U.K.’s best-selling single of 1987 and hit the top of the charts in sixteen countries, including the U.S. Astley—skinny and pompadoured, with an incongruously soulful voice—became a pop heartthrob. There were upsides to fame, like meeting his wife, who worked for his Danish record distributor, but also stuff that was, you know, weird, like the time two nuns in Italy asked him to autograph their Bibles.

Astley hated feeling like “public property.” One day in 1993, he was in a black car bound for Heathrow, on his way to New York to promote his fourth album, “Body & Soul.” He’d just said goodbye to his baby daughter, and he had developed a fear of flying. “Something just kind of washed over me, and I said, ‘I don’t want to do this anymore,’ ” he recalled. He asked the driver to pull over, called his manager in tears, and then returned home, a retiree at the age of twenty-seven.

“For about a year, I did sod all,” he said, as the crew blasted “Shower the People” through the sound system. “Fame doesn’t evaporate overnight. It takes about nine and a half months.” He’d made a “shitload of money” but had never had time to spend it. In retirement, he visited Paris and Madrid, took ski trips, ate well. His daughter, Emilie, grew up and moved to Copenhagen to study art. He recorded a standards cover album, for kicks. In 2008, he embraced his own meme and rickrolled the Macy’s Thanksgiving Day Parade from a float. (“I kind of thought, Well, that’ll be it, then.”) As a fiftieth-birthday present to himself, he recorded “50” in the man cave of his home, in East Molesey. In June, it unexpectedly débuted at No. 1 in the U.K., putting Astley back in the spotlight that he’d fled. “I get a shiver every now and again of going, What the fuck are you doing?” he said.

Did he find it ironic that his defining hit was about promising never to let people down or desert them, and that’s exactly what he did? Sipping from a glass of water, he nearly did a spit take. “I haven’t really thought about it like that!” he said. “It’s a bit weird, yeah. And the second song is called ‘Together Forever,’ so what are you gonna do?” ♦

This article appears in the print edition of the September 26, 2016, issue, with the headline “Return Engagement.”